Will you be my friend?

There's this little issue that I have experienced at various times over the years but find that it is just getting more serious the more that I move around and as I get older... Its something that military people definitely will understand as well as anyone else who frequently transplants themselves to new cities/towns.  I'm talking about the increasing awkwardness of making friends as an adult.
I was getting lunch at a restaurant today with Landon and started talking to a women who said she has a 7 month old little boy.  We chatted while we waited for our food and I wanted to ask her if she wanted to get the kids together sometime or if she wanted to join me and some other moms for a girl's night out. I found myself stuck in that strange place of wanting to be friends with someone new but feeling like I was about to ask them out on a date.
Anyone who has experienced this is already laughing right now as they relive those moments where they met someone somewhere somehow and started talking and thought "I like this person, we could hang out" but then there is that inevitable "umm... do you want to maybe get together sometime?" 
How lame do you feel?  It's like being back in junior high. What if they say "no, that's alright..." or what if, even more awkward, they think you are hitting on them (definitely a big consideration when I lived in San Francisco and even Denver).
In fact, that reminds me of a funny story about my cousin (sorry cous...).  My female cousin and I were out in Denver one night at a neighborhood bar just hanging out and talking to people and being friendly when this girl, Rose, introduces herself and starts talking to us.  My cousin (slightly tipsy and feeling friendly) responds enthusiastically and is excited that girl's name is Rose because that happens to be my cousins middle name. It was obvious to me that Rose was a lesbian but that was really no big deal. She was nice and fun and  we are always up for new friends. It was all good and innocent except my cousin (who might be a little naive on some of these matters) was being her normal friendly, slightly flirty, "two drinks- touchy feely" self.  We all hung out for a little bit then the bartender yelled out last call and we started to get ready to go.  Rose took the opportunity to ask my cousin if she wanted to hang out some other time.  My cousin, excited for a new friend since we had both recently moved to the city said of course! They exchanged numbers and we were on our way.
Well a few nights later my cousin calls me to see if I want to meet up with her and go out downtown (these were my single days- we went out a lot).  She tells me that Rose called her and they are going to go have a couple drinks and then she can meet up with me.

me: Oh really? Rose seemed like fun.  Where are you going to meet her at?  Can I just meet you two somewhere and we can all go out from there?
cousin: umm she wants me to meet her at this hotel downtown
me: a hotel?
cousin: no they have this really cool bar on the top floor I guess.  She said it has a pretty view. It should be cool!

(Now, there are  a few things I know about rooftop hotel bars, they have easy access to hotel rooms and they aren't the place that you meet up with a friend to pre-game before you go out on the town.)

me: does Rose think this is a date?
cousin: what? no! why would she think that?
me:  I don't know.  Maybe she missed the part where you were talking about all those guys the other night?
cousin: no she just wants to hang out.  She doesn't know many people I guess. She seemed fun though so why not?
me: true.  ok well go and I'll meet you in a little bit.

So about two hours later I'm getting off the elevator at the hotel and walking into a restaurant/bar that overlooks downtown Denver that is filled with business people at the bar and couples at candlelit tables along the windows.  I spot my cousin and Rose sitting together at their romantic couple-intended table. (I hold back my laughter.)
Rose who is all of 4'10" with uber short dark spiky hair is wearing a white button down, slacks, black "work boot" shoes and dramatic eye makeup and is looking a little nervous. She seems surprised to see me there and as soon as I sit down I realize she wasn't informed of the plans for the night and now thinks I am crashing her date and invading her turf.
After managing to casually mention that my cousin is my cousin and therefore family (and relieving Rose's worry that I'm stealing her date) I realize that my very straight cousin is still oblivious that she is on a date with a girl, and that Rose, even though my cousin has been talking about the guy she just broke up with, is still oblivious that my cousin is very much into men.
In an attempt to get everyone out of the inevitble awkward, I convince them that we should all go out to another bar.  Less than an hour later, as we are getting dragged into a country bar and my cousin ran into the arms of one her boyfriends, Rose finally admitted that her dream date was not happening and when my cousin's guy pointed out what was obvious to everyone else but my cousin, she finally admitted that her new girl friend thought she was going to be a girlfriend. Oopsies!